Holy Moly, I’ve Been Writing This Site For 20 Years

I started blogging one weekend day in May 2002 on a lark. I had several friends with blogs back then, and I thought I’d try my hand at it. Only I didn’t have anything truly original to say on politics and current events, which is what other blogs I knew about were doing. So I decided to write about travel and miles and points along with an eclectic amalgamation of offbeat news. I focused on what people came to me for help with and just things that amused me. I was writing for myself, not for anyone else.

My original blog site is still largely operational, showing 2003 content. I can’t access the original 2002 posts, but most of those are archived at ViewFromTheWing.com. The earliest posts I still have copies of are from late May 2002 but I haven’t searched for the first few weeks of the blog on the various online archive sites.

My Original Blog

In the beginning I’d get 30 visits a day. The very first link to this site came from legal blog The Volokh Conspiracy. Within a year I was getting 500 a day, although there were exciting spikes along the way — Glenn Reynolds of Instapundit would link to me regularly, especially for my coverage of the TSA and the early bumper stickers I created to Impeach Norm Mineta as Secretary of Transportation (the TSA had been part of DOT before it was moved to the newly-created Department of Homeland Security, by the way I still find the use of ‘Homeland’ to be creepy). The tagline for the stickers was “Liberty & Security Not Bureaucracy.”

I don’t think I was getting 2000 visits a day regularly until I was about 4 years in. One thing that helped me jump to even that level were links from my boss’s blog and an opportunity to guest blog for him.

When I look back at my posts even from those first few years I’m not super proud of them. It took me a long time to find my ‘voice’.

But it was fun. I’m not naturally a great writer, but I still love the creative outlet and opportunity to express myself. I got to interact with and even to know many readers who share my interests. In 2005 I even declared what I wanted for Christmas and a reader sent it to me. (One of only three reader gifts that I recall, I’ve appreciated them but please no gifts!)

Back then blogs interacted with each other more than they do today. Blogging was a conversational medium. You linked to someone’s post and shared why you agreed or disagreed with them. That’s how traffic was built. That formative experience for me has a lot to do with why I credit where I find things, and why I try to send traffic to blogs (by including them in lists of links) when I feel like they deserve greater attention.

This Blog is 100% Me, But it’s Only Part of What I Do

Long time readers know that I never went full time with blogging. As some of the other sites became full-fledged businesses, even selling out to corporations, this has remained one of the many things that I do. I still have a job, it’s where I get my health insurance, and I travel for work. I also write this blog; started an award booking service; help put together the Freddie Awards; consult with financial institutions on the travel and loyalty industries; and even serve as an expert witness in federal criminal trials.

I keep extremely busy, but it’s doing all of the different things that I love. Meanwhile I continue to build this blog. Everything I know or believe above the theory of the firm? I do the opposite. Along the way I became a husband and a father.

Fortunately since the blog just one of the things that I do, and everything here is in my own voice, I write on my own terms. You don’t have to like this blog, or like every post, and I respect your opinion. But I speak my mind, I stake out positions, I don’t stay milquetoast desperate to avoid controversy that might push some readers away.

That’s not smart for ‘business’ but I do just fine. Not that it even has to for me to write it. This blog started without any ads at all. GoogleAds didn’t even exist when I began. After a month or so Glenn Reynolds paid to take down the ad placed there by my first site host, Blogspot. After 7 months Randy Petersen offered to host my blog. But it wasn’t until 2004 that I had an ad up. “BlogAds” were selling on my site for $40 per week, and I told Randy he could keep it all to defer hosting costs and the technical help his team had given me to get things set up.

After more than five years of blogging I was making $250 a month from the site. It wasn’t long after that I was making $750 a month. I’m very fortunate to have done well since then, but it began simply as a labor of love and stayed that way for years. And in doing well I’m better able to remain ‘independent’ in my coverage of airlines and hotels, since I don’t rely on them for access or income.

I make money through several ventures outside of this blog, so I don’t need to do anything I’m not comfortable with to earn a living. Instead I just keep spouting off (as some of you would say) and if people are interested they’ll keep reading it, and fortunately people have and that’s the main reason I’m compensated for the work I do here.

Some Lines That I Draw

I don’t generally accept free travel or other gifts, either, however there are events I want to attend for context or content reasons that aren’t open to the general public. When I do decide to attend an event I have a pretty clear approach to those: a charitable donation that offsets anything I’ve received.

United ran a preview flight of their first Boeing 777-300ER with their new Polaris business class in it for media. There was no opportunity to buy a ticket on this flight, which is how I’ve gotten onto various inaugurals — buying a ticket like anyone else — so what I do in cases like that is make a charitable donation equal to the value of what I’ve received (even after accounting for any tax benefit).

In order to take the United flight I had to buy a ticket to Chicago and a flight home from San Francisco, and pay for a hotel room. I also donated the cost of a first class ticket between Chicago and San Francisco.

Last fall I went to Richard Branson’s Moskito Island with Bilt. I was reluctant to take the three days away from my wife and daughter, a resort without them isn’t actually fun for me, but I was interested in what Bilt was doing. And I made a donation to cover my portion of the trip’s value.

Status comps aren’t something I’m looking for either. I was once offered free Hilton status and I declined.

I don’t seek better treatment from airlines or hotels because of this blog, however I have occasionally let an airline know I’d like to take photos, because I don’t want to run into problems and get arrested. It’s never led to better service (or if it was better than it would have otherwise been, it’s occasionally still downright awful). There have been a few times where hotels Googled me.

  • Oddly at the W Doha my upgrade wasn’t as good as what many Platinums were receiving

  • At the Park Hyatt Vendome the marketing manager came out to greet me. On that stay I received the lowest category room they can assign when using a confirmed suite upgrade award. On my other stays confirming suites I’ve always done better! They told me if I wanted a better upgrade I’d have to pay for it,

    I asked whether a room ‘like the one I had last year’ was available. I was told yes — and that I could have it for an extra 100 euros per night. I declined. While some would consider the room to be worth it, I was perfectly happy with the room I was assigned. I don’t consider a single room, usually, to be a suite but it was more than adequate for my needs.

W Doha

There are a few things that I have taken. If I attend a briefing event I usually skip out on the social stuff, I’m tired and introverted and probably want to do something else it’s not so much the ethics of a nice dinner. However I have no issue taking a sandwich in a conference room to make things a working lunch. Likewise if I’m meeting a hotel executive in one of their hotels it’s not practical for me to be the one to pick up the check, though I’m usually the one who buys under ordinary circumstances.

By the way I don’t think there’s anything wrong with sponsored trips – for many it’s the best way to develop unique content and bring it to readers. I’m fortunate not to need to do it. And with as busy as I am the last thing I want is to go where someone else wants me to go, and spend time doing things someone else wants. The most valuable resource I have — now that I’m a dad, even more so than before — is my time.

For Better Or Worse It’s 100% Me

I don’t have a staff. I write everything myself and have only had about half a dozen guest posts over the course of 20 years, usually a unique experience or perspective. That means I also have no editor and nobody to bounce things off of. I’m just me and I do the best that I can to write content that interests me (the only way I could possibly still be doing this after 20 years) and hopefully engaging content and do it in a way that let’s me sleep well at night.

I still write the way I did 20 years ago, as though nobody is ready (probably not even family and friends except when I pester them to). I forget that isn’t the case, and am often surprised when something I write reverberates around the industry. In some ways that makes me better (I don’t pull punches) but in some ways probably makes me worse.

Thank you for reading. I appreciate every one of you – the folks that email me (I still try to respond to every message I get), the folks who comment (I even love the trolls), and those who just come by quietly. I suppose if I were to ruminate on my biggest blind spot it’s the comments. I wish sometimes for higher quality comments and less trolling. But they say you get the comments you deserve, and I take responsibility for that.

I’ve never been comfortable really doing anything about it, either, I’m too stuck in the early 90s era of the internet when it was supposed to be this bastion of free speech and democratization, and I’ve also seen moderated comments sections too often used as a way of hiding disagreement from what the authors have written, hiding when people point out that they’re wrong. I worry I’m not about the temptation in any given case, so I’ve only been comfortable editing or removing comments that get extremely graphic or violent or that disclose non-public information about private people.

So what does this rumination over 20 years of blogging really amount to? That I’ve had a blast doing it, that no one will stop me from getting to the keyboard each day today and in the future, and that I appreciate everyone who reads what I write whether they enjoy it, are better informed from it, or become infuriated by it. I’m so glad I fell into this one weekend afternoon all those years ago!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Congrats. I have spoken to you at some of the various flyer meetups in the past. Your blog is still the goto for me, based on the content. These programs have changed greatly since I first got started about 20 yrs ago.

  2. Congrats! Love hearing the backstory to your blogging journey. Here’s to many more years.

  3. Congrats Gary! Discovered your blog on Google Reader in its early days (2006) and it as been in my Reader/Feedly feeds since. Good or bad, enjoy your take on things! Here’s to TWENTY more!

  4. I’ve been following you daily since 2008 and enjoy the blog. Keep it up and thank you for the information and insight!

  5. Congratulations, Gary! Mrs. Fredd and I have bumped into you once or twice at “university” events, and we’ve enjoyed reading your perspectives for quite a number of years.

  6. Just wanted to say how much I enjoy your blog here, Gary. And you are being far too modest, you are a fine writer!

  7. Congrats Gary! You continue to be a source of inspiration and I greatly value our friendship. You’ve worked hard and done well, and I salute you for 20 great years.

  8. Gary
    No matter what you wrote, I always read it. Even though I may not agree with it
    You also have a great writing style and I love learning new words and usage in my vocabulary which you are a master of!!
    Thanks and keep up the good work

  9. Congratulations, Gary ! I have incredible respect for small-business entrepreneurs.

  10. My go to Blog, almost every day. Met you a number of years ago at Chicago meet, (Wonder why that one was discontinued? Maybe because Mile Point is extinct) Just look at other travel blogs, occasionally, but View is what I look at almost every day. Hope you continue for another 20 years.

  11. The naysayers may come and go, but Gary just keeps on blogging away. Congrats on a productive twenty, and here’s to more years of good info.

  12. Congratulations Gary on a terrific and informative blog during the last twenty years! Wishing you continued good health, much joy and many successes!

  13. I remember back the first time I met you at the House of Miles out in Colorado Springs
    that Randy built wondering who you were.
    A bunch of us were there some of the earlier followers participants on Flyertalk
    You are now older like many of your readers self included!
    Randy in many ways gave birth inspiration to your passion of travel/miles writing and I’m grateful to both of you for enriching my life & wisdom in travel and teachings to many of both your followers .The Thought leader of travel is perhaps now one of the ultimate travel influencers of all time in the points and miles world.I know I’ve benefited from your inside knowledge on many occasions.
    Congrats on 20 great years and here’s to 20 plus more!
    Hopefully you’ll have some wheelchair tips by then or ways to redeem miles for them

  14. Congratulations – I check out your blog almost every day, and usually learn something new. Best wishes for continued success.

  15. Hey Gary – I’ve been following you for a number of years, but really enjoyed this history of getting started. I have always appreciated the straightforwardness of you communication and love your high standard of professionalism which comes through loud and clear. Good work – thanks for sharing all of this, not to mention your knowledge of the travel industry.

  16. Aww Gary. That was a really touching post. Thanks for giving us a window into how you have operated over the past twenty years. I really appreciate your efforts. I haven’t always agreed, especially your comments about Hawaii (where I have lived for over 30 years) and the Oscar slap) but that’s OK. Please keep your blog up!!!!

  17. Congratulations Gary, I have realized from your column that you are a straight up guy, like it or not! Here is to another 20..!!

  18. Happy anniversary Gary. Haven’t always agreed with everything you’ve written (and I be definitely been guilty of taking to the comments section more often to express than disagreement than agreement!), but you run a great site, and I for one truly appreciate your dedication to the “90s free speech” ethos of your craft.

    Had no idea you worked for Tyler by the way.

    Cheers to 20!

  19. Thanks for sharing. I did not quite understand how different you were from other blogs that I subscribe to. You’ve set the bar high for ethical standards in providing information. I don’t think you mentioned here and I don’t recall. What is your “real” job?


  20. Congrats Gary! Your work continues to be an inspiration. You are also very generous with your time for budding blogs, a trait I appreciate a lot – cheers!

  21. VFTW has been a daily read of mine for many, many years. I am richer (in knowledge and savings) for it.
    As one who worked under a strict ethics policy, I especially appreciate that you don’t feast on the travel freebies and offset those you must take with a charitable donation. That enhances your credibility in my eyes.
    Congratulations, and here’s to many more daily reads.

  22. Thank you for keeping it going. While I often try to be snarky in my posts here, I truly appreciate your work.

  23. Congratulations, Gary! Your is my daily (sometimes, more) read.
    Here’s to another 20 yrs of blogging and happy travels!

  24. I am very glad that this blog is you. That is precisely why it is a pleasure to read.
    Congrats and I trust one day not too far from day I will get to shake your hand.

    To 20 more years or as long as you want.

  25. Congrats and Thank-you! Long time reader and always grateful for your news/views and insights.

  26. Congratulations. I enjoy your blog and have been reading it every day for several years now.

  27. Thanks Gary! This has been by far my favorite travel blog on the internet and I’ve learned so much in the years I’ve been following you. It has changed the way I think about how I spend my money and the best ways to maximize travel. The number of tricks you’ve shared that have enabled my family to travel on vacations we never would have otherwise all over the world is really a testament to the efforts you’ve put into this website. Keep on doing that you do!

  28. I enjoy and learn another from your blog. Hope you keep it going for another 20!

  29. Congratulations on 20 years of authoring your illuminating “View from the Wing” blog. I expect you will continue to be travel writing 20 years from now, even if you need to update your blog name to “View from the Wheelchair.”

  30. Thanks for providing very useful travel information in a confusing travel world. I have recommended you and your blog to many friends and associates. Here’s wishing you another 20 and that it still retains the perspective of fun and not a job.

    Tim B

  31. Gary, thanks for all the good things you do for all of us. It’s a labor of love, yes, and it’s appreciated by me.

  32. Congratulations! I have been reading for a couple years and always enjoy your take on things.

  33. Twenty more, heck, thirty more! There is something to read at VFTW every day. That is the amazing thing to me. Every. Day. You have entertained for years and at times provide very profitable advice. Six or eight years ago I couldn’t wait to read every possible travelblog every day. Now I have narrowed it to Gary and Lucky. I will always read what you send us Old Friend. Thanks Again

  34. Gary, I started following your blog after you wrote about Sapphire Reserve, 3 of those paid for my family to come to my wedding in Poland.
    I’ve been hooked ever since, sooo much value in your writing, like literally thousands of dollars. I love that I can look at one place and feel like the main value that’s relevant for me is going to be there.

    I hope if in the future your available time changes, you are able to get support to continue your blog. As I have said the key word from your writing for me is Value.

    Thanks Gary!

  35. Comgrats! I have learned so much from reading your blog despite being in the airline industry for 25+ years.

    Despite the negative comments when you publish them, I enjoy the quirky stories about passengers, hotel guests etc. Very entertaining!

    Keep up the good work!

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